Episode 237 – Lessons Learned from the CEO of

Rob ShallenbergerAlright, welcome back to our Becoming Your Best podcast listeners! This is your host, Rob Shallenberger – and I’ve got on our show today a great guest, Greg Spillane. And I’ll tell you just a little bit about Greg and then have him go into a few more details about his personal life, who he is and why this is going to be an important podcast to listen to – what thoughts he may have to share with us. So let me just jump right into this and give you a little background on Greg, and then we’ll start rolling with a few questions here that I have for him.  


Rob Shallenberger: So starting from the beginning, he really started his professional career as a developer – so the tech world, the computer world. Once he got rolling in things, and shortly afterward, he founded a technology company, where he bought several cloud-based products and took those to market. After they were acquired, Greg went on to lead business development with several of the top global technology consulting firms throughout the world, where he was directly responsible for generating over $250 million in revenue. And then, in 2014, Greg’s passion for building these high-growth tech companies led him back to startups where he joined Bump – and you can talk more about this Greg – as their COO. From that point, he spearheaded their eventual pivot to, which some of you may be familiar with, maybe others not. He’ll talk to us about that. And there, he maintained responsibility for all their product development, sales, marketing, and so on. And since then, Greg has led several other turnarounds in that tech space. What I also found interesting was Greg is a former D-I athlete, played on the offensive line at San Diego State. He holds an MBA from the University of Southern California’s Marshall School of Business. So, Greg, welcome to the show!  


Greg Spillane: Thanks, Rob! I really appreciate it. I’m happy to be on your show. It definitely speaks to me, just sort of my journey and kind of continued journey to personal best is very important to me and it’s just great to talk to you and be part of this. 


Rob Shallenberger: Well, you know, let’s jump into this! People are going to get a sense of who you are, as we continue to go through this podcast. Before we talk business, we have a wide swath of listeners – there’s some people who are leading Fortune 500 companies around the world who listen to this, there are other people in the education space, there are people who are raising their children full-time. So there’s a pretty wide swath of people listening to this from all different cultures and backgrounds. So, let’s start with the athletics because that’s kind of a fascinating thing. So, you played American football, and I say American football – we’re talking the 100 yards, not soccer, here, for those who are out of the US. So, you played at San Diego State, you played on the offensive line. We were briefly talking just before we started the podcast and I thought you made a couple of cool statements there. So, elaborate on that. How has athletics, how has that experience as a D-I athlete helped you become who you have today? How has that helped you become a better leader? 


Greg Spillane: Oh my gosh, yeah! No, absolutely! I look back at really my athletic background, and really, my college athletic background is probably the most pivotal moment in my life. I mean, first of all, some of my best friends in the world are still people who were my teammates and roommates in college, and there’s just such a band of brothers, of being part of a team that carries with it, but more than that, I think what sports really brings to the table is, it’s the ultimate meritocracy. And I think that that’s really important in your professional world and in life, in general. There’s nothing that’s going to ever be handed to you. And, especially in sports, if you’re not willing to work hard and train and compete and do all the things that are important for you to be able to go out there and play at a high level and sort of not get beat, you can take that to your personal life, your professional life and it really carries through. 


Rob ShallenbergerLet’s just go back to that: what would you say was your biggest lesson learned, in all of that experience? I think you said you played for five years, you redshirted as a freshman, you were around 300-ish pounds, and now you’re like 210? So, that’s great! You’re 6,5. What was your biggest lesson learned from that whole experience? 


Greg Spillane: Oh, manI’d say hard work and compete. I mean, I just truly think that that’s something that’s allowed me to be successful in my own career. I mean, it’s helped me get to where I am or to any success that I’ve had, but it’s ultimately the willingness to put in the time and put in the effort and put in the work necessary. And, to the point that you brought up, and we were talking about before we went live, I graduated high school as kind of a skinnier kid – I’m tall and I’ve got a big frame, but I was pretty undersized for Division I offensive lineman, and I had to put on about 60 pounds of mostly muscle, to be able to compete and play at that level. So that’s, obviously, dedication to your diet and weight room and working out. And then, thankfully, when I got done playing, I was able to draw most of that weight, which once again, is dedication to diet and all those different things. But I think the one thing that really came out of it is, if you want to be successful in life, if you want to do well, if you want to get the things that you need, no one’s going to give them to you. Ultimately, the work you put in is going to be the results that come out of it. 


Rob ShallenbergerThat’s fabulous, Greg! We’re writing a new book right now and I can’t share the title yet, but we were having a team meeting this morning. And one of the team members shared a comment and he was talking about the word ‘discipline’ and he defined it as “Doing what you should do, when you should do it, regardless of the way you feel.”  


Greg Spillane: Right.  


Rob Shallenberger: And if any of us are going to be successful in any walk of life, it requires discipline in that definition – doing what we should do, when we should do it, sometimes regardless of the way we feel.  


Greg Spillane: So true!  


Rob ShallenbergerI’m just thinking of all that you probably had to go through to bulk up 60 pounds of muscle: getting up at 5 am to be in the gym – you don’t want to do that, but you do what you should do when you should do it, regardless of the way you feel. 


Greg Spillane: Yeah. Do you know what’s crazy? It’s like, the things that I had to do in college, you know, you get so sick of eating! And there’s a bunch of high-profile guys that talk about it that gained a bunch of weight when they were playing football in the NFL, etc., but I lived it. I mean, the truth was like, I would eat a gallon of ice cream before I went to bed at night or I would eat a large pizza before I went to bed at night because I knew that if I didn’t eat it, I would lose a pound or two that day and I couldn’t lose that pound. I couldn’t afford to lose that pound and, you know, now that we’re all getting a little bit older, it’s the complete opposite, right? Like, I wish I could go back to college where I was literally forced to eat everything I could.  


Rob Shallenberger: Oh, could you imagine? “Hey, honey, I need to go eat a gallon of ice cream. I’ll right be back.” 


Greg Spillane: Yeah. 


Rob ShallenbergerAlright, well, let’s jump into some of the other side. You’ve got a great background there, Greg! As far as the business side, there’s so many lessons learned, just like your D-I experience could apply to so many of us, it’s great, it’s hard work, it’s getting up, it’s that discipline that we just talked about. So many lessons learned in business can apply to people, whether they’re in business or not. And so, you’ve had the chance to see a lot of different things from your perspective, especially in the tech space, but your lessons learned, your experiences will certainly apply across the board. So, one of the things is you’ve had the chance to go into a number of companies with the directive to make big changes. That’s not always easy to do. Sometimes people don’t receive you well or they’re thinking, “Who is this guy that’s going to come in here and change things up?” I mean, there’s just a lot of dynamics that go on that. You know, it’s like a head coach. Let’s go back to your football. It’s like a head coach who comes into a team and his directive is, “Hey, turn this team into a winning team.” It’s like, there’s a lot of variables that are going to go into that. So, as you approach that situation where you go into these companies, you’ve got a lot of people you’re dealing with – how do you approach winning hearts and minds in that process? 


Greg Spillane: Oh, man, that’s a great question! And that’s truly something that I think I’ve gotten better at, in my career, having done this a couple of different times. I think early on, you come in and you might have the right answers, you might have the right experience to help that company, but without the hearts and minds, you’re never going to be nearly as successful. And what I’ve found is, the first thing you need to do when you come into a new company is, realize it’s all about your people. The hearts and minds, so to speak, is the most important part of turning any company around because there are going to be some great people there and you wouldn’t be brought in if that group of people hadn’t built something pretty good. I mean, there’s definitely some problems, there’s definitely some issues but somebody made a decision that there was enough there that they wanted to bring in some outside help to kind of get them back on track.  


Greg Spillane: So, I think the first thing you need to do is you need to come in and listen. Talk to every single person on the team, really understand what they do. Most of the time, they’re going to know the problems before you do. And let them talk, let them have a voice.  


Greg Spillane: The other thing to do is, don’t ever get overly critical with the work that’s been done in the past. It’s really easy to Monday morning quarterback, so to speak, when you come into an organization and you’re like, “Oh, why did you guys do this? This was a ridiculous decision. This makes no sense. Why are we spending money on this thing?” But the truth of the matter is, you can’t go back in time and understand all the things that went into making that decision in the first place. And whether in time it’s played out to be the right decision or not, there’s probably a group of really intelligent, capable people that thought long and hard about making that decision beforehand. So give them that credit. And then, you can talk about where we need to go forward. So, I would say that, kind of my lessons learned with this is, coming into these organizations, treat the people with the respect they deserve, really open up and listen, and be appreciative and give respect to the work that they’ve put in before you came on board, and then get them on board with seeing a future vision, and then help them understand that your job is only to make them more successful in the future. 


Rob ShallenbergerThat’s really great insight, like I mentioned there, Greg. In our company, when we do training, we focus on three things: people, culture, strategy. And there’s this old saying that I know that most people probably heard but you just reminded us of that, and that is that “people don’t care until they know how much we care.” And that’s not an easy environment to be in, so I love that advice: listen, don’t critique the previous group – that’s easy to do, isn’t it? I mean, presidents are tempted to do that every time they get in the office. Governors, the same thing. It’s very easy to critique a predecessor and that is great advice! So, let’s continue building on that thought process because, you know, we’re talking about culture here a little bit. From your perspective, how important is culture within an organization? I mean, we just talked about the people. Now, let’s talk about the culture. Why and how important is that from your perspective?  


Greg Spillane: I think culture is everything. I’m a huge believer in culture. I think we’ve all been part of, whether it’s athletics or whether it’s professional or whether it’s something that’s even outside of it – we’ve been part of groups that have great cultures and you just sort of feel it and you feel that camaraderie of the group really all pulling together and feeling like we’re sort of together and we have a common goal and a common vision; and I think we’ve all been part of bad cultures, where it’s the opposite.  


Greg Spillane: So, for me, I think it’s really important to build and help build a great culture. I think the one thing I’ve also learned a little bit with my experience is, you can’t fabricate it. You can’t come in from the outside and say, “Hey, this is the culture I want to build”, and then kind of like artificially create it. I found, from my experience, that the cultures all sort of happen a little bit organically. And a lot of that has to do with the people that you hire and the type of people that you hire. You know, we used to always say something internally, that, culture has a lot to do with who you hire, unfortunately who you fire, and who you promote, right? If you have the right kind of people that you want to build your company around, and those are the people that you’re promoting, those are the people that you continue to bring in the company and their activities and the way they’re doing things on a daily basis are the things that you’re calling out and you’re showing appreciation to the rest of the team, you’re going to start to see that the rest of the group is going to start to act in that fashion. And we always look at culture as not what you do, but how you do it. You know, from my role as a leader in the organization, it’s kind of my job to set that vision or that ultimate objective of where we need to go, that strategy – but at the end of the day, it’s the culture, it’s the people that are there and it’s the ‘how they do’ things on a day in – day out basis, that’s going to determine how successful we are as a company. 


Rob Shallenberger: Yeah. And you can sense a culture within a few minutes of walking through the doors, can’t you? 


Greg Spillane: You can! You really can. 


Rob Shallenberger: I mean, it’s kind of like flipping on – since we’re talking about sports – it’s kind of like turning on ESPN or whatever Sports Network you’re going to watch; within two or three minutes of watching a game, you can get a sense of what kind of culture exists within a team, by watching the coach, the players, how they interact with each other. I don’t know if I mentioned to you, or not, Greg: I had the chance to be an F-16 pilot for 11 years and, as a fighter pilot in the Air Force, that is a high-performance culture, because the stakes are so high. If you make certain mistakes, people will die, on both sides of that. And so, I’m right with you. Culture is a huge deal. Now, there’s a lot of people listening to this that are in different walks of life. So, how do you change a culture? Let’s say you have a culture that’s already established and you want to improve it. From your perspective and experience, what are some things that people could be thinking about that would help them improve or change a culture that’s already established? 


Greg Spillane: Yeah, that’s a great question! First, I don’t think you can artificially create a culture. I think culture is going to happen organically. It’s like planting a garden. You kind of want to plant the seeds and water it and give it sunlight, but, at the end of the day, it’s going to do what it’s going to do. And then, secondly, I don’t think culture – and I think a lot of people think it is – it’s not about ping-pong tables, it’s not about a keg in the kitchen so people can drink beers, whatever it is. I don’t think that has anything to do with culture. I think culture comes down to the alignment of the team. So, making sure that everybody is pulling in the same direction. Like, what are we here to do? What is our goal? What is our purpose? What is our ‘why’? So, I think one of the first things you need to do if you want to create that culture, is put that in a place. Like, make sure that the team understands what the goal is and what the objective is, and make sure it’s clear to every single person in the team.  


Greg Spillane: And then, secondly, set guidelines of who you want to be or how you want to do thingsWhat’s important to you? Is it about teamwork? Is it about innovation? Is it about your customer? Is customer one of the most important things within your organization? And you kind of set these core values that exist within your team. And then, what you do is you kind of put the people in place, and you let them run and you let them operate. And then, like I said, unfortunately, I think a lot has to do with who you hire, who you fire, and who you promote. If your best people are the ones that are living by these core values and are most aligned to what the core of the company is, you’re going to start to see that the rest of the group’s going to fall in behind it. And then, before you know it, you’re going to have this culture that starts to form that meets this high performance that you’re looking to bring into any type of organization. 


Rob Shallenberger: The way you said that, Greg, was awesome! There’s a phrase that we like to use when we’re talking about culture, and that is, you get a sense of what a culture is like when people use the phrase ‘That’s how we do it around here!’  


Greg Spillane: Yeah.  


Rob Shallenberger: When they say, “Well, that’s how we do it around here.” Whether that’s good or bad, that’s a cultural thing. And so, when you think about the phrases for those who are in a corporate capacity listening to this, what type of phrases do you use that around? You know, ‘that’s how we do it around here.’ What does that look like? And Greg mentioned core values. That’s a huge deal. For example, a core value that I see oftentimes is ownership, the get or done attitude that you want on the team. When you touch it, you own ityou take it to completionAnd so, I agree, Greg: having that strategic alignment is one of those things that lends itself to having a high-performance culture, and that comes back to being a leadership issue. And I like the phrase that you’re using there, ‘who we hire, who we fire, and who we promote’, because that sends a message, right? Just like you articulated right there. So, it’s good for people who would be thinking about culture. What does your culture look like right now? What are your core values? Do your employees know the core values? Do they know how their roles fit into them? How do you do it around there, in your organization? And what do those look like? So, good things to be thinking about.  


Rob Shallenberger: So, let me talk about some of your lessons learned along the way. You’ve built some great businesses, you joined Bump as their COO – so, if you had to identify, let’s say, two or three of your biggest lessons learned along the way, what would those be, Greg? And they could be business-related, they could be leadership related. It doesn’t really matter. The sky’s the limit here. What are the two or three biggest lessons you’ve learned throughout your life and in these different capacities? 


Greg Spillane: Probably from a personal perspective, it’s never stop trying to move forward. And sometimes, it’s just getting the ball rolling to get that momentum moving forward. So, in other words, it’s like the old proverb. It’s like, how do you eat an elephant? And the answer is one bite at a time. And I think some people can get a little bit wrapped around the axle when they think about a goal, and that goal feels too big. It’s like, how do I do all that? And then you fall into this sort of paralysis by analysis thing. And what I find is sometimes I just need to force myself to write that first word or do that first Google search or make that first phone call. And it’s like, that’s all I’m worried about at that time, and then, I’ll find that if I do that, it leads to the next thing and then it leads to the next thing and then before you know it, you’re on your way. And so, just sitting there, thinking about all the things that need to get done, you just become engrossed in it, and then you kind of get motivated by it and then it sparks new ideas and new creativity as you start going all these different directions and you kind of move that ball forward. From a personal perspective, that’s one of the big lessons learned I’ve had.  


Rob Shallenberger: Can I ask you one question on that, Greg? When you say ‘never stop moving forward’, can you expand on that a little bit? What do you mean by ‘never stop moving forward’? 


Greg Spillane: Yeah, don’t get complacent. Constantly try to improve yourself. I still like to compete. So, we just got a Peloton bike, so it’s like me trying to get my next PR in the Peloton and getting better at that. It’s me picking up a new hobby. I just started painting. Recently, I just picked up art since this whole COVID thing hit and I was trapped in the home. I taught myself how to do oil paintings and now I’m going down that road. But, then, professionally, it’s constantly trying to be a student of the game. What’s the newest books that are out there? Who are you following? What are you trying to learn? How do you continue to make yourself better and more effective in life, both professionally and personally? 


Rob Shallenberger: Yeah, great advice! And then, before I jumped in and asked you to go back on that, you were going to talk about the professional side of things. 


Greg Spillane: Yeah! From where I sit, and maybe coming from kind of a more of an operations role to now to be more of a CEO type of role where I am today, it’s really easy, kind of lip service for leaders to sort of say stuff like, “Hire great people and get out of their way” or “I don’t like to micromanage and all that.” But the truth of the matter is, it’s hard not to micromanage and it’s hard to get out of people’s way. So, one of the things that I think I’ve gotten a lot better at, and I’ve been more successful with, is understanding when to get involved, and when truly not to. And I used to feel like, as a leader, I needed to be in all the meetings because I needed to show my team that I care and I needed to show my team how hard I worked. And what I started to realize is, actually, by me being in the meetings, I would just naturally interject my thoughts and then, of course, sometimes, when you’re the highest title in the room, the rest of the group kind of defaults to you and they get nervous, they don’t speak their way. And then, before you know it, you really are micromanaging your company, even if you’re not getting into the granular details. So, what I really try to do now more than anything, is stay at a higher level. I have a role as the CEO of my company that I need to handle, whether it’s fundraising, whether it’s PR, whether it’s getting out there selling the company, hiring, motivating, inspiring, recruiting, etc. But, if you trust the people that you have in those roles, truly get out of their way and don’t micromanage them and trust them, and let them work truly autonomously. I think that that was something that early in my career I used to say I did but the truth of the matter is that didn’t. 


Rob ShallenbergerIt’s not necessarily easy to do that, is it? Both from the professional side and even at home. Many people listening to this have children, nieces, nephews, whatever, but especially children. Kind of the same principle applies there. You know, if we micromanage their life all the way through, at some point it becomes very easy to rebel. They want to have their own input in life, and we’ve seen that with our 18-year-old now, 15-year-old son is, we have got to allow them their freedom, to point them in the right direction, set expectations that motivate them, but then allow them to stumble, trip or fall here or there. And it’s really the same in business, wouldn’t you think? 


Greg Spillane: Yeah, absolutely! Different but similar.  


Rob Shallenberger: Except you can’t fire your children.  


Greg Spillane: Yeah, you can’t fire your children, but your job as a parent is to protect your kids. That’s just what we do. You love them more than anything in the world and it’s just so hard to see them struggle or have any kind of challenges. And I talk about this with my wife all the time, about raising our kids. I grew up with a very blue-collar family. My mom was a stay-at-home, my dad is not college-educated, blue-collar guy – he ended up doing well for himself as an entrepreneur – but there were times where we didn’t have everything we wanted to have, and I think I kind of grew up with a little chip on my shoulder, right? Like I had something to prove to people, like I wanted to be able to do more than I was or that I was able to do as a kid. And I think that kind of drive has really helped me in, obviously, my athletic career, but also in my professional career. And sometimes I look at my wife and I look at my kids, and it’s like, they have just so much! And it’s not because I have so much or anything like that. It’s just, I think times have changed and there’s just more out there, there’s more available and it’s like, I kind of want my kids to have a little chip on their shoulder. I don’t want them to be entitled, I don’t want life to come that easy. I want them to be able to overcome adversity, but it’s really hard to watch your kids suffer or have a hard time. 


Rob Shallenberger: And there’s the irony. You’re talking about micromanaging. That is an approach, right? We can micromanage, but in the end, that doesn’t really allow them those opportunities that you’ve just talked about, which anybody who’s been successful in any form of life will look back and say, “Yeah, man! I remember when I stumbled there. Man, I learned a good lesson through that!” Whatever ‘that’ is. And so, as hard as it is to watch, we’ve got to allow that to happen.  


Rob Shallenberger: From the company perspective, it’s slightly different, it’s not parenting exactly, but there are certain parallels and that’s not easy to do. For those that like personality assessments – and a lot of people are familiar with the DISC assessment – if you’re a strong D personality or a strong C, that is not easy, necessarily, to step back and not micromanage. You have a way that you want it done in your mind. But at the same time, if we’re micromanaging right on top of people, that really doesn’t allow them the freedom to grow, to own, to lead. And, in the end, that’s going to stifle their productivity, creativity, and performance. It’s a great thought that you shared there, Greg, and I think that’s something we could all internalize: how are we leading our teams? Do we need to be there in certain meetings or can we pull out of that meeting?  


Rob Shallenberger: So, hey, I can’t believe it’s already been 26 minutes. That is amazing, Greg! So, as we get ready to wrap up here, any parting thoughts for our listeners? You’ve shared some great thoughts about culture, changing culture, micromanaging – some of those lessons learned – never stop moving forward. So, a lot of great nuggets that are really valuable for anybody listening. Any parting comments or thoughts? 


Greg Spillane: We have this big flag that’s hung up in my office, and it’s one of my favorite sayings. And it just says, “Give a damn!” From a cultural perspective, when I hire or just in life – just care. Have some passion, find something you’re passionate about – or if you’re not passionate about it, find a way to become passionate about it – because that’s the most important thing in life. We’re all here and we do what we do and we’re all trying to raise our families and we’re all trying to work and I hope that we’re trying to be as best as we can, but we’ve got to find a way to have that passion and give a damn whether it’s work or your professional life – and work hard at it. And if there’s gaps, get interested and get curious, and figure out how to make it interesting. But that would be my parting comment. 


Rob Shallenberger: Yeah, that’s a great one, Greg! Do you happen to have a website or any place that people could find you if they wanted to learn more about you? 


Greg Spillane: I’m not a big social guy, unfortunately. But yeah, on Twitter I’m Greg_Spillane; on Instagram I’m Greg_SpillaneBut yeah, if anybody wants to reach out to me, hit me up! I’m at It’s my email address, and I’d love to hear from people. 


Rob Shallenberger: Yeah. Awesome! Well, you’ve shared some great thoughts, Greg! So, it’s been a pleasure having you on our podcast today. And thanks for taking a few minutes. You’re doing some awesome things out there. And you never know where a thought may impact someone. We appreciate you sharing your wisdom and thoughts! 


Greg Spillane: Thanks, Rob! I really appreciate it! Thank you! 


Rob ShallenbergerAlright, to all of our listeners, thanks for listening in today. We’ll be back next week. We hope you have a fabulous day and a great week! 

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